Dating Across the Decades

We asked real women to share their insights into all the ways dating is different (and also the same) in your 20s, 30s, 40s, 50s, and 60s.
Dating through the decades photo of two people walking

Trigger Warning: This article includes discussion of sexual assault.

Is 23 too young to be cynical about dating? I kind of thought so, but the idea has absolutely terrified me for a very long time. After an absurd amount of over-analyzing and self-reflection, I realized it’s likely partly because of relationship trauma (both firsthand and what I’ve witnessed people I care about go through) and partly because of confidence issues. Plus, I haven’t felt any sort of a void in my life because of the amazing friends, family, and career I invest in daily. Still, as I’ve opened myself back up to the idea of dating—for the first time as a “real adult”—I realized I have no idea what I’m doing

Who pays for the meal? What do I wear? Do I hug them when I meet them? What the heck do I talk about? What if it’s awkward? What if I spill something? What if my date wants to kiss me and I don’t want to? What if I find someone I really, REALLY like and they don’t like me? What if someone likes me and I don’t like them back?

The stress surrounding potentially putting myself out there made me wonder if either, a) I was not ready for it, or b) if these types of questions are going to be part of the dating game forever.

After sitting down with 5 different women—each in a different decade of life (20s, 30s, 40s, 50s, and 60-ish)—I found out more about how dating changes throughout life … and all the ways it stays the same.

While these women will remain nameless, a glimpse into each of their lives will help set the scene for their responses:

A graphic of a woman in her 20sA graphic of a woman in her 30sA graphic of a woman in her 40sA graphic of a woman in her 50sA graphic of a woman in her 60s

Where do you typically meet people you go on dates with?

“School, definitely at the gym, sometimes but rarely on dating apps, or through friends.”

30s: “Just dating apps—Bumble, Hinge, Match, and recently Facebook dating—these days. Ive never had true ‘success’ from a dating app. Ive been seeing someone from a dating app since September, but its still really tricky. Back in the day Id go out to the bars, but that was not the time guys were looking to settle down. Your 30s are so hard to date. I will say to my friends, ‘Let me know if you know someone!’ and theyll be like, ‘I know one single person,’ or, I know someone who is separated but not divorced.’”

40s: “Bumble. I used to be super anti-app, but realistically thinking about how youre going to meet someone in your 40s, and in COVID, I thought, ‘Why dont I just do the easy answer?’ I like that the woman is in control on Bumble and there are lots of safety features.”

50s: “Online dating – I met my current significant other on”

60-ish: “My friends usually fix me up with someone. I did online for a month and thought, ‘Blah.’”

When you go on a first date, what do you usually do?

s pretty much always dinner. I feel like there are so many things to learn about someone over dinner!”

30s: “My preference personally is a drink. I hate the idea of a coffee date. I cant even drink a Diet Coke past noon. I dont want to drink coffee at 6 p.m. Dinner is a bigger, longer commitment. I also like to do things that are an activity, like Topgolf or something like that. That way it feels less like a job interview, just like the same monotonous questions.”

40s: “Just commit to a drink or a coffee for the first date. One guy took me on his boat for the first date and it lasted hours. I felt trapped and I didnt want to be on his damn boat anymore. I was like, ‘What was I thinking? How can I get out of this?’”

50s: “Coffee or a drink! You can always choose to go to dinner if its going well after. I also think sometimes having a drink (just one, not getting sloppy) helps take the edge off.”

60-ish: “Lunch or a coffee. I dont suggest drinks because I dont always want to assume someone drinks.”

What’s a “red flag” or deal-breaker with dates or potential dates?

“If they don
t know how to hold a conversation. Theres a difference between knowing how to talk and converse. If you dont want to know anything about me and only want to talk about yourself, were done.”

30s: “Any dating profile that mentions, ‘I’m into fitness and eating well and into someone who does the same.’ I am someone who has struggled with my weight my entire life, so seeing that is an instant turnoff. Its so superficial and you can read right through it.”

40s: “When people only want to talk about themselves or seem to only want to text. When someone only wants to talk about themselves, it makes me think, ‘Are you even interested in me or do you just see my face and decide to match with me?’ I also look for someone who is thoughtful when filling out their profile. If you dont have time to do that, youre in it for the wrong reasons. A lot of people Ive matched with seem like they just want to text and text and text and never meet up. I think maybe they just need attention. Ill usually give someone a couple days to try to make plans to go on a date before I cut them off.”

50s: “I personally wouldnt go out with someone super timid because Im so outgoing. You can tell if someone doesnt click with you.”

60-ish: “Someone who has been married/divorced many times, or divorced less than a year when I start seeing them. Ive had my heart broken a few times because Ive fallen for guys who werent ready to be fully invested in a relationship because they were not divorced for long.”

“I hate the idea of a coffee date. I can’t even drink a Diet Coke past noon.”
What’s a green flag/turn-on for you on a date?

“My mom always told me to be interested, not interesting. I try to reflect that in dating, but I also look for it. If I can tell a guy is genuinely interested in getting to know me, that
s huge.”

“Also, with the person Im with now, when I started seeing him, it didnt feel like trial and error. I could sense that we were both into each other and that wasnt going to change. Its just a feeling thats like, ‘This is easy. This is right.’”

30s: “Im very confident and know what I bring to the table. I look for that same confidence or mentality. I want someone with a plan.”

40s: “You can tell if you click with someone just by the conversation. After being on a few dates with different people, I can also tell if someone is legit pretty easily.”

50s: “Sense of humor is key for me, truly. I also like when someone asks to kiss me the first time. It shows they respect me and boundaries. Something fun Im experiencing now is chemistry. Its a pretty cool thing. When you have that, its very natural.”

60-ish: “My faith is important to me, so I like when someones values are in line with mine.”

How has dating changed between your first few relationships and the decade you’re in now?

“Guys are a lot more mature when it comes to dating than they were in high school or college. You notice them pursuing you a bit more and taking charge. They offer ideas on what to do. Plus, the conversations are more meaningful.”

30s: “More people are starting to be divorced and have kids now, and earlier on in dating, I kind of shied away from dating people who already had those experiences in their lives. But then I realized I couldve missed out on great connections with people because I didnt give them a chance. In recent years, that hasnt been such a deciding factor up front for me.”

40s: “They say, ‘Love is blind’ … but not this time. After a divorce, youve been through such hell. Even if divorce is amicable, its still hard to do. Unfortunately, when you date in your 40s, we all have some sort of damage. Someone I went on a coffee date with said, ‘We all have our baggage, but mine is just packed neat and put away.’ Love is no longer blind, and Im trying to sniff out the red flags early. Ignorance is bliss in your 20s, in your 40s you know there is baggage there, its just figuring out how bad it is and if that person has dealt with it?”

50s: “Baggage is going to be there. You and your potential partner both have it now. Im also way more myself when going on dates at this age. I dont get nervous anymore. I was getting ready for a date once and I was like, ‘Why am I not nervous?’ I realized Im way more confident in who I am now than when I was in my 20s. If they like me, they like me. If they dont, they dont!”

“Another thing that has changed since I was young is most people are much more established in their careers at this point in life. That gives the freedom for more dates and less financial stress. In terms of exclusivity, when I first started dating, you just kinda knew you were exclusive with someone. There werent ‘stages’ like today. It wasnt until I started dating again after my divorce where I had my very first ‘Are we exclusive?’ conversation with someone.” 

60-ish: “The older you get, the more everyone will be divorced. If theyve never been married, I almost think ‘What’s wrong with them?’ But, Ive never been married either. So I guess, if they havent been married, have they done enough self-reflection to understand why.”

“Another thing is that nowadays, its more normal for people to date lots of people. Thats probably because of social media and how its easier to meet a bunch of people. I love social media but it can also be a pain.”

What are you looking for out of dating at this point in your life?

“Seeing if someone has a plan or drive is huge for me. My high school relationship had none of that. I know myself and know what I want in the future, and I want someone who also has that drive … and isn
t just all talk—someone actually implementing it. As a girl, Im always looking into the future, but I also know I have time if I dont find ‘the one’ right now.”

30s: “I remember being in college and meeting the most amazing guy. We were so in love, but I thought, ‘I don’t want to be 20 years old and dating my future husband.’ When that became a possible reality for me, it scared me. I wasnt ready for that. I wanted to be independent. When I reached my mid-20s I felt more pressure, and I wasnt sure if I was ready for that. It wasnt like, ‘I don’t ever want this.’ It was just ‘I don’t want this right now.’ And then I dated a few people and when those didnt work out, I looked around and it was like all of a sudden I missed the boat.”

“I dated a guy who said, ‘I don’t feel like I can give you what you want right now.’ But then I responded, ‘When did I ever tell you what I want? You never asked me.’ He said, ‘You just seem like you have it all together (professionally, financially, personally), so Im assuming youre looking for a husband.’

“My brother and I go to concerts together and my friends and their spouses ask me to dinner. Im just looking for someone to go with me to those things. I dont need a husband right now. And Im not looking to compromise or settle just to have someone to marry.”

40s: “Someone who within the days that Im available, wants to be beside me in this thing I call life. I have vacation time and I have income so I can travel. I want a travel companion.”

50s: “Initially, I was looking for someone to do fun things with, but also someone whose faith and values align with mine and is stable, both professionally and personally. Because as much as we want it to be, life cant be fun every day.”

60-ish: “The biggest thing is a companion. The hard thing for women is that you feel like you are on somewhat of a timeline if you want to have kids. Before 35 is way different than after 35. Ive been a foster mom and have nieces and nephews, so I have kids in my life. I was never 100% sure if I wanted to be married or have kids. I think if I truly did, I would have, because Im so success-oriented and any goal I truly want to achieve, I do. Once I was past that point, I took dating less seriously.”

“It used to be, ‘If I date someone for a year and they havent said I love you,I break it off.’ Now that Im not necessarily seeing myself getting married, I dont mind as much if were having fun together because its not really ‘wasting my time.’ Im so extroverted and love meeting new people, so now Ill go out and meet someone as long as theres no major red flags because if nothing else, its a new friend.”

Do you have any dating horror stories?

“Everyone is looking for something different, but I signed up for Hinge and Match because they are supposed to be more serious, less ghosting/hookup-y platforms. Then, a guy I met from one of those apps told me on our second date that he wants to watch his partner have sex with someone else. It was hard to not be cynical for a while after that.”

40s: “One guy I met from a dating app had two truths and a lie on his profile. I figured the lie was, ‘I want world domination’ when it was in fact that he doesnt own jorts (jean shorts). What kind of a person wants world domination?”

60-ish: “One of my coworkers fixed me up with this super family-oriented guy with a great steady job he had for 30 years. He was cute but not drop-dead gorgeous which is always a good sign for me. Everything was great on paper. We went on a first date, and it was good but not great. We had a second date planned but he called and had to cancel (for a good reason), but then all of a sudden he asked me to send him a picture of me in a swimsuit. Im in my late 40s at this point; I dont have a bunch of those just on my phone. Then, he sends me a picture of him nude with only a banjo covering his private parts. I asked, ‘Who took this picture?’ to which he responded, ‘I have a tripod.’”

“Ghosting” is a huge term for the younger generations. If something isn’t working out with someone, how do you prefer it ends?

“Preferably a call at MINIMUM, but I would appreciate an in-person conversation out of respect. It would be okay to ghost if it
s someone Ive never even FaceTimed.”

30s: “When I was younger, ghosting was more of a thing and there wasnt accountability. I was pissed when it happened to me, but then I would honestly do the same thing. I wish when it happened to me someone wouldve just been open or honest if they didnt see it working out. I can usually tell anyway. At the beginning theres so much happening. If I go on a date with someone and then I dont hear from them, I know theyre not interested. I will be up-front and say, ‘I noticed we havent been talking that much, has your interest changed?’ That gives them an opportunity. You can assume so many things, and I dont want to go through a day at work stewing about not hearing from someone, so I might as well ask.”

50s: “Honesty is important. You have to say, ‘I think youre a great person, but I dont know that were for each other.’ I think a phone call is the minimum, but an in-person conversation would be preferred.”

60-ish: “This is one of the hardest things and another reason I quit dating. Because unless both people are equally crazy about each other, its either, ‘Im going to like them more than they like me,’ or, ’I want to get rid of them but I dont want to hurt their feelings.’”

“Just be honest, even if it hurts someones feelings. Do it in person or on the phone at a minimum. Id say via phone, even via text, is fine if its only been 2-3 dates.”

Do you have any advice for someone going on a first date?

“If it
s someone you met through a dating app, Facetime to make sure youre vibing.”

30s: “Date one feels so much like an interview. Theres too much pressure and anxiety that surrounds it. So unless youre completely repulsed or grossed out by someone, go out again. At the end of the day, you chose to go out with someone because you liked their personality from all the things you talked about.”

40s: “Go on a couple of dates in the same evening (speed dating). I once met someone at 4 p.m. and then had another date at 6:30 p.m. In your 40s, your time is so precious. If Im not with my kids or my girlfriends and planned for a certain night to be my date night, screw it, Im already dolled up!

“For people who have been divorced and want to get back in the dating game, you dated before when you found your first partner. I promise its not that scary. You have to let your guard down and trust your judgment. Sometimes you dont trust your judgment because you ‘didn’t get it right’ the first time, but you have to trust yourself. Its actually a lot of fun. I have so many single girlfriends dating.

“For people with kids, there is pressure to be a role model for what dating looks like. You have to be careful. If I say Im going to be home at 10 p.m., I need to be home at 10 p.m. and I dont need to be stepping inside with lipstick all over my face. I want my kids to respect themselves, so I need to make sure I do, too.”

50s: “Just do it. Life is too short. You get to meet new people and it can be safe. Even if its just for something to do. It can be fun! To feel more comfortable, talk on the phone beforehand.”

60-ish: “I dont let them pick me up on a first date, Ill meet them. Thats partly for safety, partly also because the end-of-the-night walk to the door or asking, ‘Do you want to come in?’ is always awkward the first time and Id rather avoid that.”

“Also, my mom wanted me to be independent because of my dad not being dependable, but I think she made me too independent. I didnt want to depend on anyone. I became financially independent and successful in all areas of life. My niece was living with me, and I could see she wanted to be like me. But I told her, ‘I want you to open your heart and your mind more than I ever did.’ She found a great significant other, and shes married with two kids now.

“Finally, you have the right to say no at any time. I can guarantee almost every single woman has some sort of story about sexual assault or harassment. I was in a situation where I was with a guy and I didnt feel like I could say no because I told him he could come over. I put it on myself. But thats not true. You can say no at any point in time. You dont owe anyone anything, ever.”

After talking to these women, I saw both their perspectives and pieces of myself reflected in them. I saw in them wisdom they gained both from their relationship history and from growing as individuals.

It helped me realize that baggage is something every single person has, and how someone deals with that baggage and moves forward with life tells more of a story about them and their character than the actual baggage itself.

Dating is scary and messy and fun and exhilarating at all ages of life. While some things change as you age, other things stay the same, and you never stop learning about others and about yourself through the process.

Kylie Stine is Indy Maven’s Community Engagement Manager.

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